Personal vs. Business Expenses

“Business or pleasure?”

You’ve probably heard this phrase before in reference to travel. Today we’re going to examine the same idea with respect to expenses. The distinction between personal and business expenses is super important because it has everything to do with whether you can deduct the expense on your taxes.

Let’s break it down: for an expense to qualify as a business expense, it must be all of these:

  1. Reasonable,
  2. Ordinary, and
  3. Necessary

…for the running of your business.

Reasonable Expenses

What is a reasonable expense? It is hard, if not impossible, to come up with a black-and-white test for whether an expense is reasonable. However, it is easy to come up with examples of unreasonable expenses:

  1. You pay to have gold-plated toilets installed in your company’s bathroom
  2. While doing a Costco run for coffee, you throw a steak and a bottle of red wine for yourself into the cart and put everything on the company card
  3. You book your own private vacation to Hawaii on the company credit card

Note that these items all relate to things you buy for the company or for yourself with company money. If you buy steak to share with your employees at the company potluck, it can qualify as deductible meals expense. If you reward your top salesperson with a vacation to Hawaii, this can ultimately count as deductible compensation (just note that your employee will be subject to paying payroll and income tax on the value of their vacation).

Ordinary Expenses

Whether an expense is ordinary depends on the nature of your business. Let’s say you spend $1,000 on pet food every month for an exotic menagerie of tropical birds. If you run a zoo, great! If, on the other hand, you’re a paperclip manufacturer, then look around you. Are other paperclip manufacturers keeping hordes of exotic pets? Probably not, which means that it’s not an “ordinary” expense.

The IRS does not expect you to robotically conform with your competitors. But, the IRS can step in deny the deductibility of an individual expense, or a whole truckload of expenses, if it seems like you’re doing something way off course. Your business may be extraordinary, but make sure that your expenses are ordinary. That is to say, make sure they’re common and accepted within your industry—expenses that would be expected in whatever situation your company finds itself in.

Note that usual is not a requirement. Maybe this is an expense that you will only pay once during the entire run of your business. In that case it can still be deductible if it passes all the other criteria. A good example of this might be paying someone to clear all the bats from your workplace’s attic: this is unusual, but it’s good for employee morale to not have to worry about random bat attacks.

Necessary Expenses

Maybe you’ve had the kind of meeting where your accountant asks, “Is this truly necessary?” Much like our other requirements for business expense, there is no fine line to determine if an expense is necessary. But we can look at some examples of unnecessary expenses:

  1. Hiring a shoe shiner for all of your employees…at a telemarketing company
  2. Installing a vacuum tube document delivery system in this day and age, unless you’re a bank
  3. Buying state-of-the-art gaming PCs for the office at a car dealership

If an expense could be considered “appropriate and helpful” for your business, then there’s a good chance the IRS would agree with you. An example of this might be hiring a massage therapist to set up in your break room during the busiest season of the year. Sure it might not be strictly necessary, but it certainly would be appropriate and helpful, helping to stave off burnout for your employees and perhaps boosting employee retention during a time when many might want to leave the company. Now, if you don’t have employees, it isn’t deductible unless it is a medical expense.

The Connection to Income

Perhaps a good way to determine whether an expense is business or personal, and also whether it’s reasonable, ordinary, and necessary, is asking yourself:

Does this expense help me earn income for my business, either directly or indirectly?

Of course this isn’t the end-all argument for whether an expense qualifies.

Specific IRS Rules About Business Expenses

As you saw above, the standards of reasonable, ordinary, and necessary are not crystal clear. However, there are some very specific expenses that the IRS has said are not deductible as business expenses:

  1. Commuting expenses: Unfortunately, you are simply not allowed to deduct the gas, depreciation, and parking expenses involved with commuting to and from work.
  2. Many people get excited about the idea of deducting the cost of work uniforms. The regulations on this are very strict. To perhaps oversimplify, the only clothing you can deduct is clothing that would make you look like a dork if you wore it to a social event (think of a gas station employee uniform with your name on your chest within a white oval).
  3. Gifts to customers are only deductible up to $25 per customer per year. Exception: Branded items like sunglasses, tote bags, or pens are fine to give away with impunity. Gifts to employees are fine, just know that they may need to be considered as compensation—check with your accountant (or us!) about that.
  4. The home office deduction is a topic by itself!
  5. It may be no surprise to you that bribes are not tax deductible, even if an argument can be made that they are reasonable, ordinary, and necessary.

Don’t Mix business and Personal Expenses!

Mixing business and personal expenses can land you in hot water.

Do you own a corporation or other entity that enjoys limited liability? If so, then you can lose the liability limitations of your business if you intermingle business and personal expenses. This is called piercing the corporate veil and it is very, very bad. One of the biggest reasons you set up a company, limited liability status, can be ruled out by courts if you disrespect the separation between you and your business.

In other words: If you lose your limited liability protection, then people who sue your company can come after YOUR personal savings and property!

Even if you don’t own a corporation and you do business in your own name or as part of a partnership, it is always bad form to mix business and personal expenses. If you forget to separate your personal expenses before tax time, then you may end up filing your taxes incorrectly which can lead to penalties and interest charges from the IRS.

TL;DR: If an expense is reasonable, ordinary, and necessary, and it directly or indirectly helps you earn income for your business, then it’s probably deductible as a business expense. Make sure to separate your business and personal expenses by using different bank accounts and different credit cards.

Why Are Bank Reconciliations Important?

If you’ve ever seen someone tearing their hair over a reconciliation that just won’t balance, maybe you’ve wondered what the fuss is all about. Why are reconciliations, or “recs” or “recons” as you may have heard, so important?

For the purposes of this post, we’re going to focus specifically on Quickbooks Online.

Bank Transaction Imports

Let’s lead in with something very important that bears repeating. If you are the person who imports online banking transactions into your software, then:

Pay careful attention to what you’re doing during the bank transaction import.

The bank transaction import is the first step of your bank reconciliation. If you can ensure that everything goes to the right place on the way into your books, then the reconciliation will go much easier.

Here’s a tutorial on bank transaction imports for Quickbooks Online.

Abe Lincoln once said, “Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” Doing a careful, proper bank transaction import is similar — if you’re cautious enough then you’ll often spend a lot more time on the transaction import than the reconciliation itself!


Watch Out For Uncategorized Income!

One of the most important things to look out for during a bank transaction import is to make sure that you’re not importing anything to “Uncategorized Income” unless you really mean to. Assigning items to Uncategorized Income often results in your QBO bank deposits not matching properly to the bank import.

If You Receive Checks, Use Undeposited Funds

As a bit of an aside, if you receive physical checks from customers then it’s best to receive them to Undeposited Funds in the Receive Payments screen. Then, deposit all of them together with a Bank Deposit from the “+” icon. You can think of Undeposited Funds as the virtual equivalent of your zip-up bank deposit baggie.

If you don’t do this, then your books and the bank might match in dollar amount but not in the number of transactions. For example, your Quickbooks might have three $100 deposits while your bank statement shows one $300 deposit.

The Reconciliation Itself

So you’ve spent a whole month carefully importing your online bank transactions (you do reconcile monthly, right?) and now it’s time to seal the deal. It’s time to click on that gear icon and begin your reconciliation! Here’s a tutorial on how to reconcile your bank account.

Finding the Leftovers

Reconciling is all about finding the leftovers. You start off by eliminating all the transactions that your QBO books and the bank agree on: this is probably the bulk of the month’s activity and would include most of your checks and deposits, and almost all of your electronic funds transfers.

But the real point of reconciling is to find the leftovers and examine them! What are the transactions that haven’t cleared, and why haven’t they cleared?

Common types of leftovers and examples:

Items that appear in your Quickbooks but won’t appear in the bank statement:

  • Checks recorded in QBO that haven’t cleared the bank
    • Example: You handed Employee Ned a check on the 5th of last month, but he left it in his glove compartment. Maybe it’s time to consider direct deposit, if only for his sake!
  • Deposits in-transit
    • Example: Your customer initiated an electronic funds transfer to you on the 31st and you booked it in Quickbooks, but it hadn’t hit the bank account by month-end.
  • Bank errors — in my experience this is rare, but it can happen
    • Example: The bank employee depositing a check transposed some numbers and accidentally deposited a $565 check as a $656 check.


Items that appear in the bank statement but that might not be in your books yet:

  • Errors on your company’s books — it happens to the best of us!
    • Example: Employee Ned asked for a payroll advance at the end of the day, so you pulled a check and hand-wrote it to him, but you forgot to book it in Quickbooks. Maybe he asked for the advance because he left that paycheck in his glovebox! (For the record, we recommend against handwriting checks unless that is your normal way of operating.)
  • Bank fees, penalties, service charges, etc.
    • However you like to call it, many banks like to nickle-and-dime you. Depending on how closely you’re watching your bank accounts, you might not notice these fees until you see the bank statement.

Examining the Leftovers

There are two parts to examining your leftovers:

  • First, think about the whys of this leftover. Why did it happen? It’s not always a bad thing to have a leftover, but sometimes it’s the result of an inefficiency that can cost you time or money.
  • Second, think about the hows — how will you get your books to match the bank statement? Unless there’s a bank error, you want your QBO bank account to be a mirror image of the bank statement.

Tying It All Together — Why Is It Important to Reconcile?

Okay, time to wrap all of this up. Why is it important to reconcile?

If your bank account is not reconciled, then it’s possible that your business has less cash than you think. When it comes to payroll or payables, you may end up committing to spending more money than you have available and landing in overdraft territory.

Reconciliation is one of many error-checking processes that you can use to make sure your books are squeaky-clean. An error discovered during a bank reconciliation can lead to finding other errors. For example, accidental duplicate invoices could mislead you into thinking that your business is more profitable than it actually is!

TL;DR: Yes, you need to be reconciling your books. If this isn’t your jam we can do it for you, or we can show you how in a training session.

Bookkeeping: What Should I Be Keeping Track Of?

As a small business owner, should you be keeping records or copies of:

  • Receipts?
  • Bank statements?
  • Everything?
  • Nothing?

The answer is: all of the above. You should be keeping any receipts, copies of your bank and credit card statements, and any information that will be used to prepare your tax returns.

What is Bookkeeping?

Bookkeeping is the keeping of a business’s financial records. It involves keeping track of your income, expenses, receipts, and balances in all of your accounts.

When we advise clients to follow proper bookkeeping procedure, they often ask:

  • What is the easiest way to keep track of things?
  • Do I need to get Quickbooks?
  • I have a practice management software — that’s enough, right?


The type and size of your business dictates what specific bookkeeping and accounting system I recommend you put in place.

Before recommending a system, I typically ask questions such as:

  • How many transactions a month do you have?
  • Do you have a practice management system like SimplePractice?
  • Are you keeping your receipts?
  • Do you like DIY recordkeeping or do you hate manually recording transactions?

We recommend that you put a system in place to help you keep track of all of the above. It can be as simple as saving photos of receipts in a Drive folder and updating your Excel sheet each month. It can also be as automated as taking pictures of a receipt using an app that connects to QBO so it pulls a copy into your Quickbooks file before working through your income and expense items each month.

When you are just starting your practice, using a simple Excel sheet to record your transactions works well since you tend to have more time to do things related to data entry. I also always recommend keeping copies of your receipts for business expenses for up to three years after we file your tax return.

Boom — there is an accounting system for you.

You might be thinking, “well that sounds like more work then I want to do.”

If so, we do offer some alternatives:

1Tap – $45/year

This lets you take pictures of your receipts and then creates a spreadsheet for you. When you take the picture, the software asks what type of expense it is. This is super handy for those who don’t want to do a ton of data entry or go the Quickbooks route. We have a firm license for this software so we offer it to our clients at $45/year.

Quickbooks Online – Monthly fee $20-25/mo

We recommend Simple Start for small businesses. It connects with your bank account and pulls transaction info automatically. You will need to classify each expense, but then you will be able to pull reporting to track your business expenditures and goals.

The above includes only a few options that are easily available.

TL:DR: The default answer is yes you should keep a copy of that. Setting up a recordkeeping system is an important step for your business.